Freddie Prinze Jr. on Howard Stern in 2001

Freddie Prinze Jr. Made a Bet About SMG 13 Years Ago, and He Won

In 2001, Freddie Prinze Jr. appeared on Howard Stern. At the time, Freddie was 25 years old and engaged to Sarah Michelle Gellar. As you can see in the video above, Howard Stern spent a portion of the interview grilling Freddie about the engagement. Howard insists the marriage won't last and even offers to make a million-dollar bet that the marriage won't even go 10 years. And now, 13 years later, it seems Freddie's having the last laugh. Even though the couple is notoriously private about their relationship, every now and again, we catch a glimpse of the couple's sweetest moments. And who could forget Sarah Michelle Gellar's amazing selfie, which she posted on Twitter after reaching 200,000 followers? One thing's for sure: Freddie Prinze Jr. should find Howard Stern and make him pay up.